Process for producing fluorinated methyl-benzyl alcohol

ABSTRACT

An object of the present invention is to provide a process for producing a fluorinated methyl-benzyl alcohol, which process is industrially applicable. A process for producing a fluorinated methyl-benzyl alcohol according to the present invention includes hydrogenolysis of one hydroxyl group in fluorinated benzene dimethanol. The hydrogenolysis can be carried out in a solvent in the presence of a catalyst. The catalyst can include at least one metal selected from cobalt, iron, copper, nickel, platinum, palladium, and rhenium, and the hydrogenolysis can be carried out using hydrogen.

CROSS REFERENCE OF RELATED APPLICATION

This application is a 371 of PCT/SP01/08355 filed Sep. 26, 2001, anapplication filed under 35 U.S.C. §111(a) claiming benefit pursuant to35 U.S.C. §119(e) of the filing date of Provisional Application No.60/256,918 filed on Dec. 21, 2000, pursuant to 35 U.S.C. §111(b).

DETAILED DESCRIPTION OF THE INVENTION

1. Technical Field

The present invention relates to a process for producing fluorinatedmethyl-benzyl alcohols by hydrogenolysis of one hydroxyl group in afluorinated benzene dimethanol, particularly by hydrogenolysis in asolvent in the presence of a catalyst. Fluorinated methyl-benzylalcohols are useful as a starting material or an intermediate of medicaland pharmaceutical products, agricultural chemicals or other organiccompounds. For example, JP-B-1-20143/1989 discloses that fluorinatedmethyl-benzyl alcohols are reacted with cyclopropane carboxylic acids toobtain ethers having high insecticidal activities.

2. Background Art

For example, the following processes are proposed as the process forproducing fluorinated methyl-benzyl alcohols.

1) JP-B-4-6694/1992 discloses a process for producing4-methyl-2,3,5,6-tetrafluorobenzyl alcohol by reducing4-methyl-2,3,5,6-tetrafluorobenzoic acid with lithium aluminum hydridein dried ether, and a process for producing3-methyl-2,4,5,6-tetrafluorobenzyl alcohol by reducing3-methyl-2,4,5,6-tetrafluorobenzaldehyde with sodium borohydride inmethanol.

2) JP-A-63-77829/1988 discloses a process for producing2-methyl-3,4,5,6-tetrafluorobenzyl alcohol by allowing pentafluorobenzylalcohol to react with magnesium methyl bromide in tetrahydrofurane.

3) DE-B-3714602 discloses a process for producing4-methyl-2,3,5,6-tetrafluorobenzyl alcohol by reducing4-methyl-2,3,5,6-tetrafluoro benzoic acid with sodium borohydride in1,2-dimethoxyethane.

4) GB-B-2155464 discloses a process for producing4-methyl-2,3,5,6-tetrafluorobenzyl alcohol by reducing4-methyl-2,3,5,6-tetrafluorobenzoic acid chloride with sodiumborohydride.

However, these processes are not favorable for carrying out industriallybecause of having problems in that expensive reducing agents are usedand strict moisture control for these reducing agents is required.

OBJECT OF THE INVENTION

Accordingly, it is an object of the invention to provide a process forproducing a fluorinated methyl-benzyl alcohol, which process can becarried out industrially.

MEANS TO SOLVE THE PROBLEMS

The present invention comprises the following subjects.

[1] A process for producing a fluorinated methyl-benzyl alcoholrepresented by formula (2):

(wherein m represents an integer of 0 to 3, n represents an integer of 1to 4, and m+n is an integer of 1 to 4), which process compriseshydrogenolysis of one hydroxyl group in a fluorinated benzene dimethanolrepresented by formula (1):

(wherein m and n are the same as above).

[2] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in [1], wherein the fluorinated benzene dimethanol isrepresented by formula (3)

(wherein n represents an integer of 1 to 4), and the correspondingfluorinated methyl-benzyl alcohol is represented by formula (4)

(n is the same as above).

[3] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in [1], wherein the fluorinated benzene dimethanol istetrafluorobenzene dimethanol represented by formula (5)

and the corresponding fluorinated methyl-benzyl alcohol istetrafluoromethyl-benzyl alcohol represented by formula (6)

[4] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in [3], wherein the tetrafluorobenzene dimethanol of theformula (5) is 2,3,5,6-tetrafluorobenzene-1,4-dimethanol and thetetrafluoromethyl-benzyl alcohol of the formula (6) is2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol.

[5] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in any one of [1] to [4], wherein the hydrogenolysis iscarried out in a solvent in the presence of a catalyst.

[6] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in [5], wherein the catalyst comprises at least one metalselected from cobalt, iron, copper, nickel, platinum, palladium andrhenium, and the hydrogenolysis is carried out using hydrogen.

[7] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in [6], wherein the catalyst is at least one catalyst selectedfrom the group consisting of a sponge cobalt catalyst, a modified spongecobalt catalyst, a sponge nickel catalyst and a modified sponge nickelcatalyst.

[8] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in [6], wherein the catalyst is a sponge cobalt catalyst or amodified sponge cobalt catalyst.

[9] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in [6], wherein the catalyst is a supported cobalt catalyst, asupported nickel catalyst, a supported palladium catalyst or a supportedrhenium catalyst.

[10] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in any one of [5] to [9], wherein the solvent is a single ormixed solvent comprising at least one selected from saturated aliphaticor alicyclic hydrocarbon, aromatic hydrocarbon, alcoholic solvent, etherof aliphatic or alicyclic hydrocarbon and water.

[11] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in [10], wherein the solvent is a single or mixed solventcomprising at least one selected from toluene, xylene, methanol,ethanol, dioxane, dioxolane and water.

[12] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in any one of [1] to [11], wherein the hydrogenolysis reactionis carried out in a hydrogen partial pressure of from 0.05 to 15 MPa.

[13] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in any one of [5] to [12], wherein the amount of the solventused in the hydrogenolysis reaction is 1 to 20 times by mass based onthe fluorinated benzene dimethanol.

[14] The process for producing a fluorinated methyl-benzyl alcohol asdescribed in any one of [6] to [13], wherein the amount of hydrogen usedin the hydrogenolysis reaction is 100 to 180% by mole based on thefluorinated benzene dimethanol.

MODE FOR CARRYING OUT THE INVENTION

The present invention is described in detail below.

The present invention relates to a process for producing fluorinatedmethyl-benzyl alcohols by hydrogenolysis of one hydroxyl group influorinated benzene dimethanol, particularly, hydrogenolysis in asolvent in the presence of a catalyst.

The fluorinated benzene dimethanol used as a starting material in theinvention can be synthesized by known methods. For example,tetrafluorobenzene dimethanol can be easily prepared by hydrolysis of2,3,5,6-tetrafluorobenzene dimethanol diacetate, as described inJP-A-1-238555/1989.

As the catalyst used in the invention, metal catalysts are favorable,particularly, a catalyst comprising at least one metal selected fromcobalt, iron, copper, nickel, platinum, palladium and rhenium is morefavorable.

The catalyst used may be a metal itself, a sponge metal catalyst or asupported catalyst.

The “sponge metal catalyst” used in the present invention is a porousmetal catalyst obtainable from an alloy which comprises a metalinsoluble in alkali or acid such as nickel or cobalt, and a metalsoluble in alkali or acid such as aluminum, silicon, zinc or magnesiumto thereby eluting a metal soluble in alkali or acid by use of alkali oracid.

In the present invention, it is preferred to use the sponge cobaltcatalyst and sponge nickel catalyst.

Further, a modified sponge metal catalyst obtainable by modification inthe presence of a metal other than nickel or cobalt, or a metal oxidethereof may be used in the present invention. Examples thereof mayinclude a modified sponge nickel catalyst modified with molybdenum and amodified sponge cobalt catalyst modified with manganese.

The “supported catalyst” used in the present invention is a catalystsupporting a highly dispersed fine divided metal containing at least onemetal species or metal oxide particles on a carrier such as silica,alumina, silica alumina, activated charcoal or diatomaceous earth.

It is preferred to use a supported cobalt catalyst, supported ironcatalyst, supported copper catalyst, supported nickel catalyst,supported platinum catalyst, supported palladium catalyst and supportedrhenium catalyst in the present invention.

In particular, it is preferred to use the supported cobalt catalyst, thesupported nickel catalyst, the supported palladium catalyst and thesupported rhenium catalyst.

Further, a supported catalyst, which comprises, as a main component, atleast one metal selected from cobalt, iron, copper, nickel, platinum,palladium and rhenium, further modified by adding at least one of theabove metal species or other metal species can be used in the presentinvention. Examples thereof may include a supportednickel-copper-alumina catalyst, supported copper-chromium-silicacatalyst, supported palladium-rhenium-alumina catalyst and supportednickel-cobalt-alumina catalyst.

Next, the hydrogenolysis reaction of the invention will be described.

The amount of the catalyst added in the reaction is not particularlylimited, and differs depending to the catalyst form. Generally, thecatalyst is used in an amount of from 0.01 to 300% by mass, preferably0.05 to 100% by mass, particularly preferably 0.1 to 50% by mass basedon fluorinated benzene dimethanol subjected to the hydrogenolysis.

Preferable examples of the solvent used in the hydrogenolysis reactionaccording to the present invention may include saturated aliphatic andalicyclic hydrocarbons, aromatic hydrocarbons, alcohols, ethers ofaliphatic and alicyclic hydrocarbons and water. Examples of thesaturated aliphatic and alicyclic hydrocarbons include n-hexane,n-octane, iso-octane and cyclohexane; examples of the aromatichydrocarbons include benzene, toluene and xylene; examples of alcoholsinclude methanol, ethanol, n-propanol, isopropanol, n-butanol,ethyleneglycol and propyleneglycol; and examples of ethers aliphatic andalicyclic hydrocarbons include diethylether, diisopropylether,methyl-tertiary-butylether, tetrahydrofuran, dioxane and dioxolane.These solvents may be used singly or in a mixed one containing any ofthese solvents. Further, in the case of using at least two solvents as amixed solvent, non-uniformly mixed solvents can be used. Preferableexamples of the single solvent are toluene, methanol and dioxane, andpreferable examples of the mixed solvent are toluene-methanol,toluene-water, toluene-methanol-water and dioxane-water. The solvent isused in an amount of from 0.5 to 30 times by mass, preferably 1 to 20times by mass based on tetrafluorobenzene dimethanol.

The hydrogenolysis of the present invention can be carried out byintroducing hydrogen into gas phase thereby heating to predeterminedtemperature, or by purging gas phase with inert gas that has no effecton the hydrogenolysis reaction, and heating to predetermined temperaturethereby introducing hydrogen. The reaction can be carried out at atemperature of from ordinary temperature to 250° C., preferably abovethe temperature at which the fluorinated benzene dimethanol is melting,or dissolving in the solvent. The pressure for the hydrogenolysisreaction is appropriately from 0.05 to 15 MPa by the partial pressure ofhydrogen. The hydrogen gas used in the present reaction does not havenecessarily a high purity, and may contain inert gases that have noeffect on the hydrogenolysis reaction especially.

The fluorinated benzene methanol used as a starting material accordingto the present invention is a compound represented by the above formula(1). Examples thereof may include monofluorobenzene dimethanols (such as2-fluorobenzene-1,4-dimethanol), difluorobenzene dimethanols (such as2,3-difluorobenzene-1,4-dimethanol, 2,5-difluorobenzene-1,4-dimethanol,3,5-difluorobenzene-1,4-dimethanol), trifluorobenzene dimethanols (suchas 2,3,5-trifluorobenzene-1,4-dimethanol), tetrafluorobenzenedimethanols (such as 3,4,5,6-tetrafluorobenzene-1,2-dimethanol,2,4,5,6-tetrafluorobenzene-1,3-dimethanol,2,3,5,6-tetrafluorobenzene-1,4-dimethanol), monochloro-monofluorobenzenedimethanols (such as 6-chloro-2-fluorobenzene-1,4-dimethanol),monochloro-difluorobenzene dimethanols (such as2,3-difluoro-5-chlorobenzene-1,4-dimethanol),monochloro-trifluorobenzene dimethanols (such as2,3,5-trifluoro-6-chlorobenzene-1,4-dimethanol), anddichloro-difluorobenzene dimethanols (such as2,6-difluoro-4,5-dichlorobenzene-1,4-dimethanol).

Preferable examples are tetrafluorobenzene dimethanols (such as3,4,5,6-tetrafluorobenzene-1,2-dimethanol,2,4,5,6-tetrafluorobenzene-1,3-dimethanol,2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and a more preferableexample is 2,3,5,6-tetrafluorobenzene-1,4-dimethanol.

The fluorinated methyl-benzyl alcohol obtainable by the productionprocess of the present invention is represented by the above formula (2)and corresponds to a compound obtainable by hydrogenolysis of onehydroxy group in the fluorinated benzene dimethanol of the formula (1).Examples of the fluorinated methyl-benzyl alcohol may include preferablytetrafluoro-methyl-benzyl alcohols (such as3,4,5,6-tetrafluoro-2-methyl-benzyl alcohol,2,4,5,6-tetrafluoro-3-methyl-benzyl alcohol and2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol), and more preferably2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol.

The fluorinated methyl-benzyl alcohol obtained by the production processof the present invention may be purified by separating the catalyst byfiltration, centrifugation and other operations, then concentration,extraction and/or distillation.

EFFECT OF THE INVENTION

According to the present invention, fluorinated methyl-benzyl alcohols,especially tetrafluoromethyl-benzyl alcohol can be produced by anindustrially advantageous method.

EXAMPLES

The present invention will be described with reference to the followingexamples hereinafter, but it is not restricted by the examples.

Example 1

To a 1 liter autoclave, 300 ml of toluene, 25 g of a sponge cobaltcatalyst in a water-containing state (in which the catalyst amount is 5g) and 30 g of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol were chargedand a gas phase was thoroughly purged with hydrogen, and thereafter thehydrogen pressure was set to 1.5 MPa at ordinary temperature (thepressure means gauge pressure hereinafter). The stirring and heating forthe autoclave were started and the temperature thereof was kept to 160°C. When the temperature reached to 160° C., the pressure was 2.2 MPa.The reaction was continued for 1 hr. Then, the autoclave was cooled toroom temperature. After the cooling, the pressure showed 1.0 MPa. Atthis time, the amount of absorbed hydrogen was 104 mol % based on2,3,5,6-tetrafluorobenzene-1,4-dimethanol charged. Hydrogen inside areactor was removed, and thereafter the reaction mixture was recoveredand the catalyst was filtered.

The reaction mixture was heated under reduced pressure to remove thesolvent by distillation, and further by gradually decreasing thepressure, a fraction distilled at 665 Pas at a temperature of from 100to 105° C. was recovered. The fraction was analyzed with nuclearmagnetic resonance spectrum (NMR) analysis and gas chromatography-massspectroscopy (GC-MS) to identify 98% 2,3,5,6-tetrafluoro-4-methyl-benzylalcohol.

Further, using the distilled 2,3,5,6-tetrafluoro-4-methyl-benzyl alcoholas an authentic sample, a part of the reaction mixture recovered in theabove reaction was analyzed with the gas chromatography internalstandard method. In result, the conversion of2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 94%, the yield of2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 88% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of2,3,5,6-terafluoro-p-xylene was 4% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol).

Example 2

To a 100 ml autoclave, 30 ml of 1,4-dioxane, 2.5 g of a sponge cobaltcatalyst in a water-containing state (in which the catalyst amount is0.5 g) and 3.0 g of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol werecharged and a gas phase was thoroughly purged with hydrogen, andthereafter the hydrogen pressure was set to 0.3 MPa at ordinarytemperature. The stirring and heating for the autoclave were started andthe temperature thereof was kept to 160° C. When the temperature reachedto 160° C., the pressure was 0.5 MPa. Hydrogen was fed to the autoclaveto keep a pressure at 0.5 MPa, and when the hydrogen absorbing amountreached to 145 mol % based on 2,3,5,6-tetrafluorobenzene-1,4-dimethanolcharged while watching the hydrogen flow rate, the reaction was stopped.The reaction required 4 hr.

Then, the autoclave was cooled to room temperature. Hydrogen inside areactor was removed, and thereafter the reaction mixture was recoveredand the catalyst was filtered.

The resulting reaction mixture was analyzed with the gas chromatographyinternal standard method. In result, the conversion of2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 69%, the yield of2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 40% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of2,3,5,6-terafluoro-p-xylene was 7% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol).

Example 3

To a 100 ml autoclave, 30 ml of 1,4-dioxane, 3.0 g of a supportedpalladium-carbon catalyst and 3.0 g of2,3,5,6-tetrafluorobenzene-1,4-dimethanol were charged and a gas phasewas thoroughly purged with hydrogen, and thereafter the hydrogenpressure was set to 5 MPa at ordinary temperature. The stirring andheating for the autoclave were started and the temperature thereof waskept to 220° C. When the temperature reached to 220° C., the pressurewas 9 MPa. The reaction continued for 12 hr. Then, the autoclave wascooled to room temperature and the pressure after the cooling showed 4.7MPa. At this time, the amount of absorbed hydrogen was 82 mol % based on2,3,5,6-tetrafluorobenzene-1,4-dimethanol charged.

Hydrogen inside a reactor was removed, and thereafter the reactionmixture was recovered and the catalyst was filtered. The resultingreaction mixture was analyzed with the gas chromatography internalstandard method. In result, the conversion of2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 56%, the yield of2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 37% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of2,3,5,6-terafluoro-p-xylene was 6% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol).

Example 4

To a 100 ml autoclave, 30 ml of 1,4-dioxane, 1.5 g of a supportedrhenium oxide-alumina catalyst and 3.0 g of2,3,5,6-tetrafluorobenzene-1,4-dimethanol were charged and a gas phasewas thoroughly purged with hydrogen, and thereafter the hydrogenpressure was set to 3 MPa at ordinary temperature. The stirring andheating for the autoclave were started and the temperature thereof waskept to 220° C. When the temperature reached to 220° C., the pressurewas 4.8 MPa. The reaction continued for 5 hr.

Then, the autoclave was cooled to room temperature and the pressureafter the cooling showed 2.6 MPa. At this time, the amount of absorbedhydrogen was 116 mol % based on2,3,5,6-tetrafluorobenzene-1,4-dimethanol charged. Hydrogen inside areactor was removed, and thereafter the reaction mixture was recoveredand the catalyst was filtered. The resulting reaction mixture wasanalyzed with the gas chromatography internal standard method. Inresult, the conversion of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol was83%, the yield of 2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 58%(on the basis of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and theyield of 2,3,5,6-terafluoro-p-xylene was 14% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol).

Example 5

To a 1 liter autoclave, 600 ml of toluene, 30 g of a sponge cobaltcatalyst in a water-containing state (in which the catalyst amount is 6g) and 60 g of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol were chargedand gas phase was thoroughly purged with nitrogen. The stirring andheating for the autoclave were started and the temperature thereof waskept to 160° C. The pressure at this time was 0.28 MPa. Hydrogen wascharged to the autoclave to increase the pressure to 0.53 MPa. Then,hydrogen was further fed to the autoclave to keep the pressure at 0.53MPa, and when the hydrogen absorbing amount reached to 130 mol % basedon 2,3,5,6-tetrafluorobenzene-1,4-dimethanol charged while watching thehydrogen flow rate, the reaction was stopped. The reaction required 30minutes.

Then, the autoclave was cooled to room temperature, gases inside thereactor were removed, and thereafter the reaction mixture was recoveredand the catalyst was filtered.

The resulting reaction mixture was analyzed with the gas chromatographyinternal standard method. In result, the conversion of2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 99.5%, the yield of2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 82% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of2,3,5,6-tetrafluoro-p-xylene was 11% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol).

What is claimed is:
 1. A process for producing a fluorinatedmethyl-benzyl alcohol represented by formula (2):

(wherein m represents an integer of 0 to 3, n represents an integer of 1to 4, and m+n is an integer of 1 to 4), which process compriseshydrogenolysis of one hydroxyl group in a fluorinated benzene dimethanolrepresented by formula (1):

(wherein m and n are the same as above).
 2. The process for producing afluorinated methyl-benzyl alcohol according to claim 1, wherein thefluorinated benzene dimethanol is represented by the formula (3)

(wherein n represents an integer of 1 to 4), and the correspondingfluorinated methyl-benzyl alcohol is represented by formula (4):

(wherein n is the same as above).
 3. The process for producing afluorinated methyl-benzyl alcohol according to claim 1, wherein thefluorinated benzene dimethanol is tetrafluorobenzene dimethanolrepresented by formula (5)

and the corresponding fluorinated methyl-benzyl alcohol istetrafluoromethyl-benzyl alcohol represented by formula (6)


4. The process for producing a fluorinated methyl-benzyl alcoholaccording to claim 3, wherein the tetrafluorobenzene dimethanol of theformula (5) is 2,3,5,6-tetrafluorobenzene-1,4-dimethanol and thetetrafluoro-methyl-benzyl alcohol of the formula (6) is2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol.
 5. The process forproducing a fluorinated methyl-benzyl alcohol according to any one ofclaims 1 to 4, wherein hydrogenolysis is carried out in a solvent in thepresence of a catalyst.
 6. The process for producing a fluorinatedmethyl-benzyl alcohol according to claim 5, wherein the catalystcomprises at least one metal selected from cobalt, iron, copper, nickel,platinum, palladium and rhenium, and hydrogenolysis is carried out usinghydrogen.
 7. The process for producing a fluorinated methyl-benzylalcohol according to claim 6, wherein the catalyst is at least onecatalyst selected from the group consisting of a sponge cobalt catalyst,a modified sponge cobalt catalyst, a sponge nickel catalyst and amodified sponge nickel catalyst.
 8. The process for producing afluorinated methyl-benzyl alcohol according to claim 6, wherein thecatalyst is a sponge cobalt catalyst or a modified sponge cobaltcatalyst.
 9. The process for producing a fluorinated methyl-benzylalcohol according to claim 6, wherein the catalyst is a supported cobaltcatalyst, a supported nickel catalyst, a supported palladium catalyst ora supported rhenium catalyst.
 10. The process for producing afluorinated methyl-benzyl alcohol according to claim 5, wherein thesolvent is a single or mixed solvent comprising at least one selectedfrom saturated aliphatic or alicyclic hydrocarbon, aromatic hydrocarbon,alcoholic solvent, ether of aliphatic or alicyclic hydrocarbon andwater.
 11. The process for producing a fluorinated methyl-benzyl alcoholaccording to claim 10, wherein the solvent is a single or mixed solventcomprising at least one selected from toluene, xylene, methanol,ethanol, dioxane, dioxolane and water.
 12. The process for producing afluorinated methyl-benzyl alcohol according to claim 1, wherein thehydrogenolysis reaction is carried out in a hydrogen partial pressure offrom 0.05 to 15 MPa.
 13. The process for producing a fluorinatedmethyl-benzyl alcohol according to claim 5, wherein the amount of thesolvent used in the hydrogenolysis reaction is 1 to 20 times by massbased on the fluorinated benzene dimethanol.
 14. The process forproducing a fluorinated methyl-benzyl alcohol according to claim 1,wherein hydrogenolysis is carried out using hydrogen in an amount of 100to 180% by mole based on the fluorinated benzene dimethanol.